


Tailored Heart

by Kool_Operator



Category: Undertale (Video Game)
Genre: 1920's, Alternate Universe - Mafiafell (Undertale), Alternate Universe - Mobtale (Undertale), F/M, Loosely based of the 1920's lol, Mobtale - Freeform, Other Additional Tags to Be Added, Seamstress, Sewing Puns, Slow Burn, Youre a seamstress/tailor, ive had this idea forever and no one else wanted to write it so i /guess/ i have to do it, mafiafell, well slow for you, which can come quite in handy for someone who dodges bullets all the time
Language: English
Status: In-Progress
Published: 2020-05-25
Updated: 2020-10-17
Packaged: 2021-03-02 23:01:18
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 5
Words: 8,697
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24374689
Author URL: https://archiveofourown.org/users/Kool_Operator/pseuds/Kool_Operator
Summary: You're a seamstress stuck in a rundown part of town during the Depression. You're a good girl that doesn't get into trouble almost to the point that your life is teetering on the edge of monotony. You don't go looking for trouble but trouble finds you and he's is wearing a fine tailored suit.
Relationships: Sans (Undertale) & Original Character(s), Sans (Undertale) & Reader, Sans (Undertale)/Reader, Sans (Undertale)/You, Sans - Relationship
Comments: 27
Kudos: 299





	1. Chapter 1

"Thank you again, it looks good as new." The elderly woman kindly thanked you as you handed back the stitched up flower-patterned dress that had acquired loose stitching and few tears, but was an easy fix on your part.  
"No problem Mrs. Buckner, you never want such a beautiful dress to go to waste," you winked at her and she gave a little wave before leaving out the front door of your shop, the small bell ringing throughout the store. You turned around and started to clean up your workstation when you heard the bell jingle again. "Already back Mrs. Buckner?" you teased as you turned around to greet the old woman, she probably forgot her glasses again.

…

Except it wasn't Mrs. Buckner. It was a skeleton. A tall skeleton. A bean pole if you had to describe him. Long skinny legs clad in black pinstripe slacks and a matching suit jacket, black under shirt and bright red tie. You couldn't help but admire the perfectly tailored suit, the fabric and the craftsmanship made your sewing heart swoon, oh if you could work on such high-quality garments such as that...Back to the skeleton, his face was also long with sharp cheekbones and teeth, and where his eyes were supposed to be, small red pinpricks that overlooked the shop in an almost bored look. 

You were surprised to see a monster in your shop, not because you never seen a monster (the whole world had been introduced to monsters six years ago and was soon blended into human society) but monsters tended to stick in their part of the city and it is even more rare to see one in your shop. 

The skeletons arms were professionally folded behind his back and scanned the small shop before his red dots landed on you. There was an awkward pause as you both stared at each other, you remembered you mouth was still open, and you promptly shut it. You also remembered it was rude to stare so you smiled politely and faced him fully.

"Hello, is there something I can help you with?" Pause. He continued to look you up and down. You awkwardly cleared your throat and you realized that you were all alone in your empty shop with a stranger that looked like he could step on you and snap your neck with ease. 

He seemed to see what he wanted, and he started walking up to your desk, looming over you with at least an extra two feet above your head. You started to sweat, you were positive that he could fit one of his hands easily around your neck.

"Are you Y/N?" His voice was higher than you would have imagined but still had an edge that meant business.

"…Yes?" He raised an eyebrow (eye bone? His face was surprising animated for a skeleton). 

"I have been told you are a competent seamstress." It wasn't really a question, so you weren't sure how to answer.

"Umm…y-yes?" Another pause. Suddenly, a flurry of fabric flashed across your field of vision and landed unceremoniously on the counter. You looked down and saw a suit jacket. He must have been holding it behind his back this whole time. It was huge, it couldn't have been his own, too wide and not long enough. The jacket though…had seen better days. You could tell it was covered in several small tears and holes. However, you couldn't really tell what had caused theses tears, each was a different size, some were more of a cut, some were a complete hole.

"I was hoping you could fix up my brother's jacket. He has a real tendency to…be sloppy and ruin his perfectly good clothing. And since he is so lazy I, the Great and Terrible Papyrus, have to be the one to get them fixed." The skeleton, Papyrus, said with annoyance but even you could tell it was mostly for show. 

You poked your finger in the biggest of the holes, right above the breast pocket on the left side, your eyes growing big as you tried to figure out how you would fix that. A small tear here and there isn't such a big deal and your normal clients didn't mind a noticeable seam in their everyday clothes, but these suits weren't just an old flowered dress. 

You bit your lip in worry and looked up at Papyrus about to say that he's better off getting a new suit but he beat you to it.

"I understand the skepticism, but we have a special occasion tomorrow evening and he has to wear this jacket and I simply cannot get a new jacket in time." The tone in his voice told you that your shop wasn't the first he's been to today.

"Umm, I can do my best. A lot of these are actually easy to repair. But this one-" you prodded the hole in the jacket again. But Papyrus cut you off.

"Money isn't a problem." The way he said it told you that you really were his last option and you were going to do it whether you wanted to or not.

…

"What time does it need to be done?"

"My brother will be here to pick it up at 5 o'clock sharp." You swallowed nervously, you were going to have to start on this tonight. You took a deep breath through your nose and gave your best customer service smile.

"I'll see what I can do." The skeleton didn't move. "...It'll been done. " You hoped it would be anyways. Papyrus looked at your face closely and then straightened back to his full height. Jeez he is tall. And with a slight nod the skeleton monster walked out of your store, the bell jingling after him and you were left with the suit jacket in your hands wondering how in hell you were going to pull this off.

**Notes for the Chapter:**

> Papyrus: I have an impossible task that needs to be done in less than 24 hours and if you don't do it I'll be big mad
> 
> Y/N: ¯\\_(ツ)_/¯ 
> 
> Next Chapter: Sans!  
> Just a heads up I don't know /that/ much about tailoring/sewing and this obviously isn't going to be super realistic to the 1920's era.


	2. Chapter 2

**Notes for the Chapter:**

> So this chapter ended up changing a lot. Everything seemed to be going too fast so I'm slowing it down a bit. We're in for the long haul baby.

You had to admit, even with the short deadline and very small possibility of fixing this jacket you savored the fact that you were actually using your skills on such a fine piece of garment. Not that you didn't use your skills every day, but fixing a button on a shirt or taking in (or out) a couple inches at the waist on a pair of trousers just didn't feed your craving to create beautiful clothing. Not that you could blame your customers though, we were all facing an economic disaster and people were more worried about finding their next meal than trying out this year's latest fashion trends. Anyways, the people who could afford such things weren't going to come into your shop of all places, you weren't even the skeletons first choice.

At first glance the jacket seemed more like a clump of old fabric but now that you were inspecting it closer you could see how well-crafted and just how _expensive_ this jacket must have cost. It was an all-black, drape cut style, made out of thick wool and the lapels were actually lined with a soft black velvet. Something caught your eye, on the inside of the collar there was a sloppy hand stitched word that was definitely not done by a professional. _Red_. You wondered if that was the brothers name, kind of a funny name you thought to yourself. 

You made quick work of the small wear and tear around the seams and made sure to not leave a trace of your work. Deep down you were glad you've done so much repair work in the last year as you were even impressed with yourself. You also couldn't help but gawk at the amount of fabric that was used, the man must be huge! There also seemed to be a slight lingering smell of…mustard?

You laid the jacket out across your work station, the end of the sleeves hanging over the edge of the desk. The hole right above the breast pocket stared back at you in mockery. You couldn't just sew it back up, even a loss of one inch of fabric will create wrinkles in the torso area and eventually loosen the seams around the arm. 

…

In defeat, you dramatically fell into your chair looking at the jacket and that stupid hole. Who would even do this to such beautiful clothing. You looked at the clock and saw you didn't have much time, the brother was coming in less than an hour and if he was anything like the first skeleton, you were sure that he was expecting no less than the best. 

You wracked your brain for an idea when you noticed something.

…

The bell above the door gave out a shrill jingle as you were finishing up the last stitches. You looked up over your sewing machine, a pin sticking haphazardly out the side of your mouth. If you weren't already expecting a skeleton monster to come into your shop today, you might have gasped. 

He was tall. Not as tall as Papyrus but still a lot taller than you. He was wider too, but in a stocky, strong-man way. If you thought Papyrus looked like he could snap your neck with ease this guy wouldn't have to try at all. His skull was much rounder and had a lazy but almost menacing smirk that was filled with pointed teeth. A golden tooth laid in the corner of his mouth, the light from the shop's windows bouncing off it elegantly. Similar to Papyrus, his eyes were small red pricks of light that lazily scanned the store. He wore a bright red dress shirt, black tie and black vest and slacks that matched the jacket (You were sensing a theme with these skeleton brothers). 

"Hello." You said with your normal customer service voice, standing and brushing off your smock. "You must be Papyrus's brother?" The skeleton looked over from where he was looking, the dusty mannequins sporting (now outdated) dresses and mens attire. He eyes seemed to linger and slowly move up and down your body, his smile growing just a bit wider.

"An' you must be the beautiful seamstress my brother was talking about." He said with a voice that was much deeper than you would have imagined and smoother than any silk you've ever worked with. 

You sputtered at his straightforwardness, you could feel a blush already creeping towards your cheeks. He let out a short laugh as he saw the look on your face.

"Ha! Don't look so shocked angel, I'm sure you get compliments like that all the time." He shoved his hands in his pockets as he sauntered over to the counter. When he realized that you were still standing there with a dumbstruck look he rubbed the back of this head, the confident exterior slipping just slightly. "Jeez, dollface, I didn't mean to scare ya or anythin' I just was shocked to see such a beautiful young dame here…When my brother said you'd be a lady I was thinking some type of spinster granny type, ya know?" 

You blinked a couple times before letting out a small chuckle. 

"It's alright…I was just…caught off guard a little bit." You could still feel the blush burning your cheeks.

Silence as you both tried to navigate through the awkward tension, luckily the brother recuperated a lot quicker than you did. 

"Well, now that you know how I feel 'bout ya. I should probably introduce myself. The name's Red." He purred as he held out his hand, multiple chunky golden rings shining just a bright as the golden tooth in his mouth.  
You couldn't hold back a small giggle as you politely took his hand. You were right. 

"I know." You quipped smugly, relishing in the small surprised look from Red. 

"Oh so you already know me? Well I can't say I'm surprised I 'ave a pretty big reputa-"

"It's on the jacket."

…

Red let out a loud bellow of laughter, even going to the extent of wiping away a nonexistent tear. Do skeletons even have tears? It was impossible to not laugh along with him.

"Oh man, sorry ya' had to see my handiwork, I'm sure you've seen children do betta'." 

You lead him to a corner of the shop that you used as your "showroom" that only consisted of a small pedestal and a full-length vanity mirror. You silently guided him on the pedestal with the jacket in your arms. 

"I must say your brother really put me to the test, the jacket wasn't exactly an easy fix." You talked as you helped Red put on the jacket.

"Oh Boss is so dramatic, the jacket's ancient, should probably recommission another anyways."

You both stopped as you both looked into the mirror to assess the product. 

The jacket fit him perfectly, every stitch and seam laid perfectly across his broad shoulders and all your work was hidden from sight. Ironically you were proud of that, but you digress.

"Wow…It actually looks decent, uh what I mean is I haven't seen it look this good in a long time. Heh." He twisted and turned in all three mirrors before something caught his eye and you watched closely for his reaction. "A flower?"

"It's quite the rage these days." You said coolly. A bright red rose blossomed right over the hole, completely hiding it from sight. You can't really say you went out on the limb with your choice of flower color, but you let out a small sigh of relief when you saw everything match. "Also…" You reached up to gently pull back some of the petals to reveal the missing patch of fabric. "I had to somehow cover this up. How do even get a hole here?"

Red did a small take before giving you his devilish smirk again.

"Sometimes the ladies grab me a little too roughly…You know how it is. Can't get enough of me," He finished with a wink. An obvious lie but you suppose it wasn't your place to ask in the first place. "You know…I think I just might incorporate these in my everyday look, really shows my sensitive side." 

He ran his hands down the front of the jacket, giving himself one last once over before stepping off the pedestal right in front of you. 

"You are very talented Miss…?"

"Y-Y/N" You stuttered. You weren't sure why you were suddenly so nervous. Maybe it was the fact that Red was standing so close you had to crane your neck up to see his face. Or maybe it was because you couldn't quite read his expression. 

"Y/N." He hummed in thought. "Well I s'pose I should pay you fer your service?" He grabbed a wallet out of his pocket and from the small glimpse you got, the man was loaded. If you pooled together every one of your neighbor's money and put it in a pile it still won't be as much as he had in his wallet. He silently thumbed through some bills before handing you a small stack of cash. Your eyes grew wide as you looked down at the bills.

"Uhh..This is…This is way too much it's only-"

"Oh don't give me that dollface, hard's day work deserve an honest pay." He shoved the bills into your hands like it wasn't the most cash you've seen in months. You scrambled to not lose a bill as Red leaned down. "You can also think of it as a down payment for my new jacket."

You blinked and a soft smile spread across your face. Your mind raced with excitement at the hint of a new project. 

"So you'll be back?"

"Oh sweetheart, it's going to be hard getting rid of me."

**Notes for the Chapter:**

> Red: Hey baby u cute ;)
> 
> Y/N: *brain short circuits*
> 
> Red: oh shit I broke her
> 
> \-----  
> It's probably going to be a little longer for the next chapter as now I have to rewrite a lot of stuff but should be out within the week!


	3. Chapter 3

True to his word, Red came back two weeks later. You were almost embarrassed at how fast you whipped your head towards the door when you heard the familiar jingle of the bell. Ever since Red walked out of your door, you've been excitedly waiting for him to return and you were starting to think he either forgot about you or didn't actually mean it when he said he wanted you to make him a new jacket.

Red swept in with the confident aura that shrouded him the last time you saw him. Red winked when he caught your eye, that wolfish smile pulling a little harder at his cheeks when you both locked eyes. 

"Heya, sweetheart." Red cooed.

You resisted the urge to squirm under his stare and stood up from your work bench, smoothing down your hair as you walked up to the front counter. 

"Welcome back, sir. I almost thought I wasn't going to see you again." 

"Just Red, dollface." Red said with an almost tired tone under his breath. He took off his hat and jacket, hanging them up on the coat rack next to the entrance. You couldn't help but see a slowness to his movements that caught you slightly off guard. "And while I can't say seein' ya' all excited to see me ain't rufflin' my feathers, but I really didn't mean to keep you waitin' darling."

"Oh don't worry about it," you sighed teasingly, resting your chin on your propped hand. "It's not like I'm going anywhere." You said as you vaguely gestured to the empty store. "Plus, I'm sure a man like you has a lot of important business to tend to." 

You saw him chuckle, shaking his head while he said something under his breath.

"I'm sorry what was that?"

"Oh, just saying I'm 'sew' excited to get this new jacket." You blinked at his statement. Did he just make a joke? Doesn't matter, you were at work and he was your customer. Stay professional Y/N.

"Oh I apologize." You shook your head and stood up straight, slightly embarrassed by your casual manner. You didn't know what it was about Red, but he made you want to be everything your mother taught you not to be. Maybe it was his flashy jewelry or flashy smile, but you wanted to stop being the timid and meek seamstress that sat in her shop until you really did become the old lady spinster. 

"You're right. We should get down to business." You put on a more professional smile and casually pulled out a giant leather book. A loud thud rang through the shop and you wasted no time pulling back the pages, each one covered in several sample fabric swatches. Ignoring Red's shocked expression, you flipped through page after page, your eyes excitedly looking over each one full of different materials and colors. 

"Now we should start with a material. I have wool, flannel, mohair, tweed, oh, maybe we can do a plaid-"

"Woah woah woah, slow down there, sweetheart." Red interrupted you as he laid a hand on yours, stopping from your frantic page flipping. "There's something I need to tell ya. Ya' see, this isn't just some jacket…It's, uh…like a club jacket…So it's gotta match the other one's you know?" Red look slightly nervous, hoping he wasn't hurting your feelings. 

"Oh." You paused, looking down at his hand on top of yours. It was surprisingly warm, and a small buzz ran up your arm. Perhaps it was the magic that monsters held within their bodies, something that not many people got to see up close. In fact in many public places the use of magic was strictly forbidden.

"Actually, that's going to make this really easy!" You flipped expertly through the pages again, except now it ended on a page with finality. You pulled out a few of the swatches that seemed similar to the original. "How do these look?"

"Imma be straight with ya' sweetheart, I can't tell the difference between any of these, my brother's more 'clothes minded'." He admitted casually with a small laugh.

You laughed along and stepped out from behind the counter. 

"Let's get your measurements."

…

This definitely wasn't the first time you've taken someone's measurements, but this was the first time it felt…intimate. It also didn't help that you needed your own step stool to reach the top of his shoulders, now making you both eye to eye. You both fell into a comfortable silence that was only interrupted when you asked to lift or lower his arms. Even though you were focused on your work, you kept catching Red's stare in the mirror, quickly looking away each time. 

After taking the basic measurements you started pinning the suit template over Red's clothes.

"Let me know if I accidentally prick you." You mumbled as you pinned the pattern around his shoulder together to get a better tailored fit.

"From you? I wouldn't mind." He said casually, not moving and only looking at you from the side.

You sputtered, a second time he's done this to you.

"Y-you forget yourself." The heat in your cheeks was instant and you tried to re-focus at the task at hand. Maybe if you poked yourself with a needle you could focus on the pain instead.

At that he turned his head and your faces were only a few inch apart. You couldn't contain the small intake of breath as the pin in your mouth dangled dangerously between your teeth. 

"…Perhaps. But I'm kinda liking the way you're makin' me feel angel." Red's face was suddenly very serious, and he slowly reached up one of his hands to tuck a stray hair behind your ear. You were frozen, whether from fright or something else, you couldn't tell. Was this a prank? His forwardness was most unusal to anyone else you've ever met. Not to mention you barely knew each other. "Ever since I walked through that door, I can't get you outta my head…I would like to see you again. Except maybe not in such 'professional' circumstances?" 

"I-" And the sound of that stupid bell rang through the store. Both of your heads turned at same time to see good ole Mrs. Buckner looking thoroughly surprised. 

You felt rather than heard the sigh leave Red's chest and when you looked back at him, his casual smile was back, his eye sockets half lidded in a relaxed posture. 

"I actually should get going. Promised Boss I'd be home for dinner, wonder what it'll be tonight." He talked as he carefully rid himself of all your pins and patterns, gently putting them in your hands. Then he turned to you with his back to Mrs. Buckner.

"Perhaps we can finish our conversation later." He whispered as he produced a small card from his pocket. The words 'Red Gaster' with a phone number underneath plainly printed. You stared at the card as Red went to the front of the shop. After grabbing his hat and jacket from the coat rack he tipped his head and hat at Mrs. Buckner.

"Ma'am." And he left without another word.

Both you and Mrs. Buckner stood there in silence, you still staring at the card in your hand and Mrs. Buckner squirming with awkwardness. The old lady let out a small cough to grab your attention.

"Well…he's…very tall."

**Notes for the Chapter:**

> I just wanted to say thank you to everyones wonderful comments, you guys are all awesome.


	4. Chapter 4

**Notes for the Chapter:**

> Sorry for the wait :P
> 
> I literally do not have any excuse.

You fiddled with the card and kept looking back and forth between the phone and the medium size box that held the finished jacket. 

The last few weeks was…interesting. The usual quiet of your shop was comforting but now all you could think of was him. His eyes, the timbre of his voice, that golden tooth catching the light. It was slowly driving you crazy and you kept telling yourself to keep it together. You barely knew the man, you won't let a few nicknames and sweet whispers in your ear turn you into a feebleminded maiden that fawns over any man that looks her way.

It also didn't help that Mrs. Buckner came in almost every day since asking about the mysterious skeleton. Yesterday she thoughtfully brought you lunch and quickly started her interrogation again as soon as you sunk your teeth into the cheese sandwich. 

"Now what was that fella doing here again?" She asked politely as she carefully sat on one of your stools. 

"He was just getting a new jacket." You quickly said between your chewing. You could see her purse her lips in thought. 

The woman acted like she was your mother. You didn't mind of course. It was nice to have someone looking after you when you had a hard time looking after yourself. You met her when you first opened your shop, four years ago, when she came to you in frustration about 'getting a stupid button back on her husband's shirt'. The arthritis had gotten so bad in her hands that the preciseness in hand-sewing, let alone threading a needle, lead her to you. Luckily, it blossomed into a one of a kind friendship.

"Well what does he do?"

"I don't know, I don't really ask that kind of thing." You quickly took another bite to avoid saying anything else. 

"Well, you better be careful, missy. Men like that are always up to no good," you both knew what she meant by that. Criminal. While your little shop offered a sense of safety and peace, the streets outside were getting more dangerous and closer to home. But you wouldn't judge a book by its cover, besides Red hadn't done anything to make you think he'd hurt you…

"And a monster…" Mrs. Buckner gave you a distasteful look and you let out a soft sigh. As much as you didn't want to admit it, not everyone was as open-minded as you when monsters came to the surface and tensions between both humans and monsters were still high, neither trusting the other. 

…

You flipped the business card through your fingers again, Mrs. Buckner's words going through your head. You couldn't help yourself but be perplexed by this man. You knew he was bad news. Your whole life you've done a good job staying out of trouble. You were smart and worked hard to get to where you are now. And even if your body was enjoying the adrenaline of dealing with something dangerous you knew nothing good come out chasing that feeling. 

You looked down at the number again. Why were you nervous? You were going to ring him up and tell him to pick up his jacket and that was it. He would move on to something more interesting and you'll be back to your boring, simple life. 

Before you could change your mind, you grabbed the phone and dialed, your finger holding on the last number before letting the dial swirl back its original position. After the second ring you wished no one would actually pick up the phone but alas by the fourth ring a voice abruptly roared from the other end.

"Hello?" A familiar voice but not Red's. "Who is this? Speak now or I will end the call." Papyrus coldly spoke on the other end. 

"H-Hello. This is Y/N from Simple Threads…I'm, um, calling for Red..?" You stuttered and you were met with a silence that reminded you of the first time you met Papyrus. 

"…Ah yes. The seamstress. You know, my brother seems very fond of your…sewing skills. He can't seem to stop-" At this you hear a scuffle on the other end of the line and you wait in stunned silence. 

Eventually the ruckus subsides and a slightly out of breath Red comes on the line. 

"Heya sweetheart, sorry you had deal with Boss, he just says the darnedest things heh.." 

The silence was thick between the lines and you were glad that he couldn't see the raging blush on your face. What was Red saying about you?

"Ahem, I was just calling to inform you that your jacket is finished and ready for pick-"

"Oh! Perfect timing angel. You know I was thinking maybe you could bring it around tonight" He kept rambling on and on and in your mind you started to panic, this wasn't the plan. 

"Actually-… Uh I think-" 

"Sadly, I'm pretty busy now but maybe around 7? Let me get you the address."

"Well, actually-"

"You gotta pen an' paper sweetheart?"

You blanked and then sighed.

"…Yes." You grabbed a nearby pen and spitefully wrote down the address. This was it. You were just going to go over there, drop of the package, and leave. And you were going to especially ignore the small butterflies swirling in your stomach.

…

You stood in front of the mansion, the weight of the box becoming heavier. You triple checked that you had the right address. It took you two buses and a 10-minute walk to find this place and the last thing you were expecting was this. A manicured lawn with monsters in fine dressings running around in a hurry, holding this and that. You knew Red was wealthy but this was…this was a lot to take in. 

Just who was this man.

…

You walked up to the giant doors and wrapped your jacket around you tighter out of comfort and to try to block out the late fall breeze. Knocking on the door seemed like a death sentence and you wondered if you should just leave the box on the doorstep and leave before anyone noticed you. 

You were just about to go through with that idea when the door opened slightly, revealing the ever so tall Papyrus, wearing the same jacket that laid in the box you were holding except his was long where Red's was wide. 

"Oh…He invited the human, how lovely." He deadpanned as you both stared at each other.

"Um, actually, I'm just dropping this off no need to-"

"Sans, get your lazy bones in here!" Papyrus barked. Sans? Suddenly, Red appeared in the doorway. He was wearing matching outfits to Papyrus minus the jacket. As soon as he saw you his face lit up in surprise, almost like he wasn't expecting you to actually show up. 

"Sweetheart! You made it just in time. Please come in, it's freezing out there. Don't let Boss scare yah, he's all bark." Red grabbed your arm gently yet firm as he dragged you in to the house. 

Your complaint never left your mouth as your body was engulfed in a wave of warmth and light. You looked around in awe, the interior was expansive and elegant with deep red accents spread throughout. The marble floor shined under your feet and beyond the foyer you could see a large room with monsters in similar clothing to the ones outside as well as ones with more fine dresses and suits. The sounds of a band warming up piqued your interest as you looked over the many different types of monsters, the sparkly dresses and slick suits and some things in between. 

"-ya want?" You swiveled your head back to Red, a little embarrassed that you were caught staring, you didn't want him and Papyrus to think that you were judging. 

"Sorry what?" Red chuckled under his breath before nudging his head towards the direction you were staring at. 

"I can take ya over there if ya want? Band's 'bout to start, maybe do a lil' dancing?" The smirk he gave was mischievous.

You shoved the box into Red's chest quickly, catching him off guard as he let out a little 'oof' and wrapped his arms around the box. 

"Perhaps another time, I really shouldn't over stay my welcome." You politely said while taking a step back towards the door where Papyrus seemed to be taking guard over. 

Red looked a little hurt but quickly recovered as he set the box on a nearby side table and started to undo the ribbon wrapped around it.

"Well hold on there sweetheart, gotta at least make sure the thing fits, right?" He asked pointedly looking at you and you sighed as you stepped back in front of him. He slowly pulled the lid off and took his time as he scanned the jacket. "Well no holes, that's a good start." He commented, and it took all you had in you to not roll your eyes. He continued to look over the jacket until something caught his eye. 

"Ha! Guess I don't have to do it myself this time." He grinned as he held up the inside of the collar towards you, an elegantly hand sewn name in red thread brandishing the fabric. You felt your cheeks burn at his find. 

"I-uh, just wanted to spare you the trouble…" 

"You didn't want me to ruin it." Red said knowingly. Not _totally_ untrue. You smiled sheepishly, luckily Red didn't seem offended. 

Wordlessly, Red finally slid on the jacket, the fabric gliding over his vest and undershirt and finally settling perfectly on his torso. 

"How do I look?" He asked coolly. 

"Presentable for once." Papyrus jabbed behind you just as you had opened your mouth to reply. Red shot him a look, but Papyrus just continued to lean against the wall. You quickly walked up to Red, pinching the sleeves and pulling at the fabric to make sure it was all the right lengths. 

"Now, I left some space to work with, so I can still alter if need be." You went straight into to tailor mode as you check the seams to make sure they weren't pulling in places that weren't supposed to and straightening the lapels, flattening them with the palms of your hands. At this you felt Red stiffen and you quickly pulled your hands away, embarrassed at what probably looked indecent to any passerby. 

"Ahem, well, it seems that it fits, I, um, should probably be going…" You wrapped your jacket tighter even though the heat of the house was making you sweat. 

Red seemed to snap out of his haze as he rushed forward to gently take one of your hands. "Oh, but the party just started, you can't leave yet. Besides, you came all this way it'd be a shame to leave now without some grub?" 

Red's skeletal face somehow looked innocent, like a child wishing on a star, and when you opened your mouth to decline his offer, your stomach answered for you, making the loudest growling sound. I guess cheese sandwiches haven't been really cutting it. At that, Red's innocent face slowly morphed into a grin that was almost terrifying, like the cat that caught the mouse. 

"Ya, eva' had monster food?"

**Notes for the Chapter:**

> Papyrus: Ah look my brother has a crush
> 
> Papyrus, a sibling: I'm gonna ruin this whole mans career
> 
> \------
> 
> Next Chapter- Party Time!


	5. Chapter 5

**Notes for the Chapter:**

> This was a really hard chapter to write but now that it's out of the way hopefully it will go a lot smoother :P

You wiped away a bead of sweat from your forehead as you took another sip of your drink. The taste was almost too sweet, but you were more concerned with the fact it was also a bright, almost glowing, purple. When you had asked Red if there was alcohol in it he gave a look of fake offense, 

"'Course not, ya' know that stuff's illegal" he said while knocking back a glass in one chug. You waited for the liquid to pour out from his nonexistent throat and drip all over his clothes but to your surprise not a drip was wasted. Red gave you a wink when he caught you staring, wiggling his fingers in a mock spooky gesture and whispering '~Magic~'. 

You were still on your first glass but you could tell your cheeks were getting rosy. Which wasn't helping your embarrassment as you tried to hide your work clothes under your jacket, the elegant and classy outfits around you not going unnoticed. You watched the purple swirl in your glass wondering how you got yourself in this situation. 

...

The rest of the time Red had you at the ongoing food table that held an assortment of foods, a lot that you've never even seen before and some that you thought you knew but had some weird monster twist. 

"Real spiders?" 

"I swear they taste betta' than regular doughnuts. Muffet's the real deal... Just don't tell 'er you don't like 'er food, you don't want to get caught in that web, trust me."

You passed on the doughnuts but the aroma of all the food was making you salivate and you dug in, much to Red's delight. The thought of filling your stomach with something more than Mrs. Buckners cheese sandwiches was enough to give yourself an excuse to stay just five more minutes. 

As you ate Red stayed by your side, cracking jokes and keeping pleasant company. You were grateful that he was keeping his distance, only resting a hand on your shoulder when he told a rather unfunny pun that he thought was hilarious, bending over and wiping away a non-existent tear. The more you drank the more you seemed to laugh back, more than the polite chuckle at least, and you even got to throw a few back at him. 

"Did you hear about the monster whose whole left side was cut off?" Red asked.

You heard this one before but you raised your eyebrow in question.

"It's okay. He's 'all right' now." He said nonchalantly, waiting for you to laugh at his cleverness.

"Yeah but I hear he's half the man he used to be." You said with the same nonchalant-ness Red had said his own punchline with. 

You watched as Red opened his mouth to continue his joke when he finally registered your sentence. His mouth stayed agape as he looked over you with a look you couldn't quite figure out what meant. You felt a little pride in stumping him at his own game.

Red's face broke back into a soft smile. He looked like he was going to say something when another familiar skeleton came up behind him and put a hand on his shoulder. Papyrus whispered something that you couldn't quite hear and then turned to leave, only giving you a glance of what might have been annoyance. 

Red looked back at you and jabbed a finger behind him towards the stage, you noticed the band seemed to be wrapping up.

"Eh, gotta show face now. Not that it's really my thing, but-" Red must have seen the panicked look on your face as he quickly raised his hands in comfort. "Not to worry though, just be a sec, dollface."

Your eyes darted around the room, reality crashing back down as you were in a room full of strangers, some particularly looking back at you with unsavory stares.

"Don't worry, no ones gonna mess with ya, sweetheart." He put his hand on your shoulder again, this time, you didn't mind it. "I promise."

He turned you back towards the food table, keeping his hand on your shoulder. "Why don't'cha have 'nother slice of pie. I'll be back before ya finish it." With that Red, slid towards the stage where his brother seemed to be waiting impatiently. You couldn't help but miss the warmth of the hand that left your shoulder. 

…

You slid the piece of pie on your plate, not that you really wanted it, but it gave your hands something to do. The irony did not fall short on you as you silently wished for Red to come back. 

You continued to stand as every table had at least one person sitting at it and you were not about walk into that minefield of trying to make conversation with strangers. 

Eventually, you saw Red and Papyrus walk on the stage, standing on either side of a podium that was recently put there. Their stances were very proper, albeit Red seemed a bit more relaxed compared to Papyrus' ramrod posture, with their hands behind their backs as they faced the crowd of people. You had to admit their matching outfits made them look very posh, and a swell of pride bloomed in you as you looked over Red's jacket and saw it no different to Papyrus's. 

Your eye caught movement and you stared as a third skeleton walked on the stage and stood behind the podium. This skeleton was interesting…While somewhere between the other two skeleton's height, he towered over the podium, resting his hands atop in a very confident manner. You could tell that he had giant holes in his palms but it didn't seem to bother him. His skull was smooth except for the two scars that ran from the top of his head to his left eye and from the bottom of his right eye to his mouth. He looked out to the crowd with a pleasant smile, his red eye lights scanning over everyone.

"Good evening, everyone." While his voice was a deep baritone, it seemed…broken? Like he wasn't used to speaking. You looked over at Red and he winked at you.

"I would like to start out by saying thank you to everyone showing up and celebrating our sixth year of monster freedom." You mentally kicked yourself for forgetting the date and not saying anything to Red nor Papyrus yet. "Before I start, I would like to thank the Letto's for joining us tonight," you followed his outstretched hand towards a small group in the way corner of the room which consisted of, much to your surprise, humans. You counted five of them, two of them of what looked like bodyguards. The man in the middle had graying hair but his eyes looked sharply along the crowd. He raised his glass to the monster on stage but even you could see the stiffness in his movements. In fact, all the humans looked on-guard. Even the beautiful woman beside him stayed on, what you assumed, her husband's arm. Her face was lax with boredom, but by the way her fingers tightened around her husband's bicep every time a monster so much looked in her direction, she was uneasy. "..I look forward to the many years ahead of our co-inhabitance." 

Your eyes confidently glazed over the rest of the crowd now that everyone's attention was towards the monster speaking. You watched as a giant dog monster slip a playing card from his jacket and into his hand while the rest of the table had turned their heads towards the front. You also watched a muscular fish woman with fiery red hair not-so-subtly follow a scared looking bird monster into another room. 

"Enjoying the pie, young one?" A soft voice behind you gently asked. Despite its sweetness there was a strange unpleasantness that lingered at the edge of the speaker's voice. You quickly turned around, roughly swallowing the half-chewed piece of pie much to your dismay. 

Before you was a rather large monster, taller than Red, covered in white fur and if you had to guess, mostly resembled a goat. She wore a beautiful purple dress with sheer, billowy sleeves and an expensive looking gold necklace with a strange symbol carved into it. Her eyes…Her eyes were a bright red but it wasn't the color that disturbed you, there was that unpleasantness again, peaking out behind the warm smile. 

You didn't want to be rude, so you returned the smile and discreetly wiped you mouth of crumbs. You were a bit intimidated but, luckily, it didn't show through your voice,

"I do, I never would have thought butterscotch and cinnamon to go so well together." 

She gave a delicate giggle behind a gloved paw. "It's the family recipe, it was my children's favorite."

Your eyes widened in realization, and silently thanking the heavens that you didn't say anything in offense.

"I can see why. You make a lovely pie, Miss-um?"

"Oh! How rude of me. You can call me Toriel, and you are?"

You gave her your name and politely shook her paw, which engulfed your hand but was still very gentle. You continued to converse, even telling her about your business, which she seemed to be very excited about. Perhaps it was a good thing you stayed after all.

"So, are you with the Letto's? I mean no offense, my child, but I haven't seen you here before."

"None taken, I'm not with them, I'm with-" You bite your tongue before the next word fell out. "I'm just a friend of Red's, he invited me." You saw Toriel's eyebrow raise slightly before she gave you another smile. 

"Red? Well, it's good that he has such a wonderful friend. Stars knows he-"

"Well look who it is. Enjoying the party Tori?" Red spoke beside you. You couldn't help but jump, you didn't even hear him come up behind you. In fact, when you looked behind you no one was on the stage anymore and some of the crowd looked to be dispersing. You looked up at Red to see him staring at Toriel with a smile that seemed a little too tight. 

Toriel looked at Red with a bit more subdued surprised, breaking into her usual gentle smile, but something behind her eyes changed and suddenly you felt like taking a step back. 

"Of course, Red. Your brother always knows how to host a perfect party. Plus, I got to have such a lovely conversation with your friend." 

Two things happened then. Toriel settled her eyes on you and you realized that the motherly gaze was gone and replaced by an unhinged stare that made shivers run down your neck. Then, Red settled his hand once again on your shoulder, except this time you were grateful for the contact and you were able to let out the tiny breath you were holding. 

Luckily, some of the tension was broken when an even larger goat monster appeared by Toriel. He was taller than even Papyrus but wider than any monster you've ever seen. He wore an all-black suit with a purple flower on his lapel. His cufflinks sparkled in the light and your jaw about hit the floor. Solid gold cufflinks with an imprint of the same design that was on Toriel's necklace.

"Toriel, honey, we can leave now, if you're ready. Oh Red! There you are, I was looking for you earlier," His eyes slid over to you, sadly, his gold cufflinks couldn't take away the tiredness from eyes and you almost felt pity for the monster in front of you. He looked exhausted. "But, it looks like you've had your hands full, perhaps we'll speak another time. Now, I think I'd like to go before I fall asleep standing up. Again!" The monster let out the loudest bark of laughter and you laughed along awkwardly as you felt Toriels eyes still staring at you and Red staring at Toriel. 

"Have a good night, yer Majesty." Red said curtly. Your Majesty? The monster grabbed Toriels hand and tugged it a little. Toriel finally blinked and looked at the monster beside her, giving him a reassuring smile. 

"Yes, I think that sounds nice." And with one final glance back at both you and Red. "Have a wonderful evening, Y/N…Red." 

Red watched them leave and continued to stare in that direction even after they were out of view. You waited awkwardly, the hand on your shoulder getting a bit too tight for comfort anymore.

"…Red?" Nothing. You cleared you throat. "Red."

Red's head whipped towards you and for a split second you saw a shadow of anger cover his face but you blinked and it was gone and replace with that charismatic smile. 

"Ya miss me, sweetheart? I told you it'd only be a sec'." You rolled your eyes and shrugged off his hand. You smirked when you caught his pout.

"I was actually just beginning to enjoy myself." You teased, not able to hide your smirk as you also started making your way towards the exit. Your feet were killing you from standing so much. 

"Oh, you wound my soul, sweetheart." Red strode next to you, shoving his hands in his pockets. "Ya'know for a second there I woulda said you actually had a good time?" He side eyed you as he lit a cigar as soon as you both stepped outside.   
The cool air was much appreciated against your rosy cheeks and you took a moment to watch the red smoke escape the skeletons mouth and billow into the night sky. 

"Earlier you said 'your majesty', that couldn't have been-"

"The King and Queen of Monsters? Yeah. They don't always come to these shindigs but it seemed we got lucky tonight, huh?" The last part dripped with sarcasm but you didn't comment on it, more occupied with the thought that you just had such a casual conversation with one of the most powerful monsters ever. 

"Don't think too hard about it, sweetheart. Everyone likes ya, you're sweet as _pie_." 

"Now that was bad." You laughed as you shoved Red in the arm while he gave you a shit eating grin. 

You both fell back into a comfortable silence and watched as a drunk bunny monster sloppily made his way across the lawn with several other monsters trying to steer him in the right direction. 

"I did." You stated. Looking over you saw Red giving you a quizzical gaze. "Have a good time, I mean. Thank you for letting me join your celebration…Even if I didn't have much of a choice." 

Red let out a laugh full of smoke and rubbed his skull sheepishly.

"Yea, well…" He took one last drag of his cigar before flicking it away. Then his voice got low, "I like having my way." You mentally chastised yourself for blushing, but hopefully it was dark enough not to be noticeable. 

"…I should get going." Was all you could get out.

"Heh, yeah…Lemme walk you to your car." Red started walking towards where you assumed where everyone parked their cars.

"Oh, I took the bus." Red stopped in his tracks before slowly turning towards you.

"How do you suppose you gonna get home, dollface?" You opened your mouth to state the obvious when it clicked. The last bus was at 10. You quickly looked your watch. 10:51. You didn't even realize you had stayed that long, and the thought of walking all the way back to the shop made you shiver from dread. 

Luckily, Red stopped your train of thought. 

"Need a ride, sweetheart?" The look on your face must have said a lot because Red turned back around and continued on his previous path. "C'mon." And you silently followed.

…

Red walked up to a sleek black vehicle and opened the back-passenger door. 

"Ladies first." He said with grandeur. You flashed a smile and moved to get in the back. 

"Sans." You both whipped your heads towards the voice and your eyes landed on the host of the party. Like earlier, you didn't even hear him approach but here he was, standing there with his arms crossed and a rather blank face. You couldn't help but notice how different he seemed compared to earlier. The posture, the aura, all different. 

"Wings." Red replied. "…Can I help ya with something?" He added when Wings didn't reply.

"I need you back at the house. Family meeting." You looked back and forth between the brothers, trying to read the situation.

"Can't it wait, I'm kinda in the middle of-"

"I'm afraid not. Tell your little friend that you won't be able have your nightcap this time." Your ears burned from the insinuation and if you weren't completely gob smacked by the thought you might have corrected him. 

Red stared at his brother for another moment before letting out a terse sigh and turning to you, blocking your view of the other skeleton. 

"Sorry, sweetheart. Maybe next time." He said flatly, gently pushing you the rest of the way into the car. 

"But, how-?" 

"Don't worry, RP will get you home safe." His hand lingered on your shoulder once again. "I promise."

With that he shut the door and you looked to the front of the car, only to find it already occupied with a cloaked figure. They didn't say anything but they did tip their head in greetings. You looked back out the window and Red and his brother were already gone. With a small lurch, the car started to move and you watched as the mansion became smaller and smaller before finally disappearing.

**Notes for the Chapter:**

> Y'all after reading this chapter: Yo when she gonna stop talking about shoulder touching?
> 
> Me, completely touch deprived: https://images.app.goo.gl/GW6daysfPnq8oYD88
> 
> \------
> 
> lmao I hope u enjoy, ur guy's comments and kudos mean the world to me while i try to navigate this story *blows kiss*


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